Be the Trendsetter: Letters to a Teenage Girl

Let me first say this: I was not a fashionable teenager. To be honest, I’m not sure any teenagers are… The ones I see who are trendy look totally ridiculous. I think your school becomes your own little world, and whatever is cool there, you think is cool everywhere.

Which isn’t actually true.

Any kid who’s been moved from city to city while in middle and high school can tell you that. One brand is hot in one city, and kids in another city have never even heard of it.

But what happens is the one kid who has the balls to wear something new and be confident in it is the one who sets the trends. I’m not talking about the kids who dress purposely ugly (goths spring to mind), ridiculous (Uggs in the summer? Really?), or skimpy (enough said).

I’m talking about that girl who seems to wear whatever she likes, and then everyone wants to wear it too. That girl. Be that girl.

Here’s what I’ve figured out about following trends.
They aren’t you, and you’ll feel uncomfortable and look uncomfortable in them.

When I was in high school, around 10th grade, I finally came around to “normal” clothes after an ill-advised stint in novelty t-shirts and big jeans. I started dressing like all the popular kids. In those days, it was khakis from The Gap and Doc Martens sandals. It wasn’t me, and I still didn’t really fit in. I didn’t figure it out until much, much later in life. I never looked good in them because I never felt good in them.
Not all trends are all that flattering.

(Bubble skirts pop into my mind.) Pick clothes that actually look good on you. I kept trying to pick clothes that looked like what I saw in magazines or catalogs, but they looked horrible on me. My mom would do this thing when she took me shopping, where she would pick up something I didn’t like and say, “Humor me.” Which loosely translated means, “Go try this on or you’re not getting anything.” Then, if it looked good, she would say, “That looks so becoming on you.”

Becoming on you. Not really the words every teenage girl is dying to hear in the dressing room. But she was onto something. There are lots of beautiful clothes out there. Just because you put them on, doesn’t mean you’ll look beautiful in them. It doesn’t mean there’s something wrong with you. It just means that some clothes look good on certain shapes, lengths, and sizes of woman. There are some clothes that just don’t look good on anyone. Period.
Pick stuff you like, whether anyone else likes it or not.

Now, this piece of advice, I sometimes followed and sometimes didn’t as a teenager. Sometimes I followed it to my own detriment (like the Star Wars athletic tee I wouldn’t take off for most of age 15), and sometimes I didn’t follow it, also to my detriment (see above, where I wore clothes because they were trendy).

The times in my life I remember enjoying my style, and consequently felt the most confident, is when I wore what made me feel good. A lot of times it included really, really short hair, which didn’t always thrill my mom and certain types of boys, but I pulled it off because I felt good in it. I actually kind of rocked the short hair.

Cultivate a personal sense of style.

I spent a lot of time trying to look exactly like things I saw in magazines and catalogs, but that stuff passes. What’s hot today isn’t hot tomorrow. And then you wasted money on clothes that aren’t cool anymore. And you just got them like, last month. (I still make this mistake sometimes. That’s why I have 5 embellished t-shirts in my closet that I just got 6 months ago and probably won’t wear ever again.)

You’ll find items that you’ll literally cry over when something irreparable happens to them. I’m not talking about materialism; I mean pieces of clothing that you feel like are a perfect representation of you and your own style, that make you look and feel great. Look for things like that, and hang onto them.

The girls I remember wishing I could look like weren’t following trends or letting what everyone else was wearing dictate their style. Well, they weren’t trendy anyway. There was just something about them… they were comfortable, they owned their look, and most of them probably still do today, over a decade later.

Find your own clothing personality, and live outside of the trends. Ironically, this will make you the trendsetter.

Thanks, Sam! I’m really glad to have found the inspiration to write something that might resonate with people again. I think the toughest time any human being ever has is as a teenage girl. It’s also the most impressionable time, I think. It’s when a young woman starts forming her self image – no easy task. I’m hoping that by saying all the things I wish someone had told me, it can take a little bit of the pain out of it.

[...] This post was mentioned on Twitter by Holly Hoffman, samdavidson. samdavidson said: As dad to a daughter, I'm totally digging and looking forward to @hollyhoffman 's series "Letters to a Teenage Girl" http://bit.ly/f0MtPU [...]

I love this, Holly! And am so psyched that you’re back to blogging here again, I’ve missed these posts! You offer practical advice that any teenage girl should adhere to, but I couldn’t help but chuckle thinking of myself at that age. Even now, when I’m out shopping with my mom, she’ll hold something up, and before I can roll my eyes or make a face or grimace, she’ll say “just try it on.” And I’ll try it on. And I’ll love it.

Mothers do know best, don’t they?

I was never the trendy type, either, but I never really wanted to be. I knew what clothes I felt comfortable in — conservative with an edge. Probably too prim and proper compared to the scantily clad fashions they’re wearing these days (do I sound like an old lady yet?), but cardigans, dress pants, boots, tanks — these were the staple of my wardrobe and I haven’t changed very much since.

I think you’re right on — it’s all about being comfortable with yourself, knowing yourself. After that, everything falls into place.

What a great post. I was always the girl who kind of stuck out because I never really wore what was “in” or fasionable. Primarily because we couldn’t afford it but I wasn’t aware of that at the time so I just had my own style, creating things out of whatever I could find. I was never very self conscious until high school when my weight kind of got away from me and all the sudden being the funny, quirky girl wasn’t enough. I love this post though because it reminds me that the awkwardness doesn’t last, and now when I look at my daughter in her completely free of inhibitions, picking out her clothes based on which dolls she is playing with (strawberry shortcake or tinkerbell) and the combo’s she comes up with, I feel like I have another chance, by encouraging her to stay happy and creative I am making up for my own insecurities, kind of like my own letter. Thanks Holly! Great post!

Hey Holly! As a recently-turned adult, who was (only a couple of years ago) awkward in the ways of fashion I can say this is solid advice. It takes a while to work out not only what your style is, but what suits your body shape and flatters you, doesn’t it?

My Mum still picks things out when she goes shopping with me and says “Just try it on.” It’s how I found my Year 12 Ball dress.